Roadmapping — Part 3: Milestones

5 min readNov 7, 2023

By including milestones, you create a sense of transparency and accountability, ensuring everyone involved is aligned and informed about the product’s journey.

This post was originally published on Roadmap Weekly.

What are milestones?

Imagine playing a video game like Zelda, where you must complete different challenges or levels, each with its own boss, before you reach the final boss. Roadmap milestones are like the special abilities you collect after each boss level. They’re the markers that show you’ve beaten a tough challenge or acquired a new skill that will help you defeat the final boss. Each milestone opens up new possibilities, reminds you how much you’ve accomplished and motivates you to keep going until you reach the ultimate victory!

What are milestones for?

Milestones aid in communicating progress to external stakeholders, investors, and customers, instilling confidence in the project’s development and demonstrating its viability. By including milestones, you create a sense of transparency and accountability, ensuring everyone involved is aligned and informed about the product’s journey.

To receive new posts and support my work, consider becoming a free or paid subscriber.

Who are milestones for?

Internal Teams: Milestones keep internal teams motivated and focused by showcasing progress and achievements, fostering a sense of unity and direction.
Stakeholders and Investors: Clear milestones build confidence and trust among stakeholders and investors, providing concrete evidence of project progress and indicating a promising trajectory.
Customers and Users: Communicating milestones to customers generates excitement and loyalty by highlighting new features and improvements, enhancing the overall user experience.
Partners and Collaborators: Milestones ensure transparent communication and alignment among partners and collaborators, serving as benchmarks for joint project progress and success.
Regulatory Bodies and Compliance Entities: Meeting milestones related to legal and regulatory requirements demonstrates adherence to industry standards, ensuring compliance and upholding credibility with regulatory bodies and compliance entities.

By catering to these stakeholders, milestones are vital in fostering transparency, trust, and collaboration throughout the product development process and its broader ecosystem.

When to create milestones (what qualifies)

Milestones on a roadmap should include critical achievements such as:

the launch of a Minimum Viable Product (MVP)
significant feature releases
user acquisition targets
integration successes
funding rounds
partnership milestones
regulatory compliance goals
user engagement metrics
scaling achievements
and revenue or monetization targets.

These milestones are crucial progress markers, demonstrating the product’s growth, market viability, and user satisfaction while indicating the product’s development trajectory to stakeholders and team members.

Anything with a significant business or product impact can make it on your roadmap as a milestone. If these milestones are known in advance, you can plan the rest of your roadmap around them and ensure you’re leaving enough wiggle room to hit these deadlines.

How to show Milestones on your roadmap

Distinct markers or symbols: Use different markers or symbols, such as flags, stars, or specific icons, to highlight and differentiate milestones from other roadmap items.
Chronological order: Position milestones chronologically along the roadmap to illustrate the sequential progression of crucial achievements and provide a clear completion timeline.
No timeframe, just a date: Milestone markers do not span a timeframe; they denote a specific date a deliverable is expected.
Concise labels: Provide clear and descriptive labels for each milestone, outlining the specific achievement or event it represents, ensuring all stakeholders can easily understand the significance of each milestone.
Colour-coded indicators: Implement a colour-coded system to differentiate milestones from other roadmap elements, enabling stakeholders to quickly identify and comprehend the critical milestones without excessive scrutiny.
Interconnected dependencies: Display any interdependencies between milestones and other roadmap items, demonstrating how each milestone contributes to the overall progress and success of the project.
Accompanying notes or descriptions: Include brief notes or descriptions accompanying each milestone to provide additional context and detail, helping stakeholders grasp the broader significance and impact of each key achievement.

Example of milestones on a roadmap

Considerations with Roadmap Milestones

Here are a few more things to consider before adding Milestones to your roadmap:

A milestone is a big commitment: Milestones are often communicated widely with internal and external stakeholders well in advance, and significant consideration should be given to what dates you publish.
Be confident: Add feature milestones after the groundwork is complete, and you’re sure you can hit those deadlines.
Build a buffer: Provide lots of leeway into the work leading up to a milestone and work backward from your milestones when planning your development roadmap.
Latest date possible: Choose the end of a quarter rather than a specific date in the quarter if you can. It’s often acceptable to have big wins and desired outcomes by the end of the quarter, so don’t schedule those deadlines any earlier if possible.

Milestones are generally unavoidable on any roadmap. You’ll have to add one at some point, whether for a much-anticipated feature release or due to external factors or demands. Be sure to keep some of these recommendations in mind when adding milestones to your roadmap and avoid the potential pitfalls of poorly planned deadlines.

This post was originally published on Roadmap Weekly.